CHM 2210 Problem Set 9
Due: November 17th, 2008
S. A. Miller
KEY
Name: _______________________
student#
Multiple Choice (1 point each)
score/20
letter
(1) The best leaving group out of the following is
(A) OH(B) NH2(C) H2O
(D) CH3CH2O-
C
(2) Which of the following is a polar aprotic solvent?
(A) CH3CN
(B) butanol
(C) H2O
(D) tetrahydrofuran
A
(3) Which ordering correctly ranks the following cations from least stable to most stable?
(A) 1°alkyl > methyl > 3° alkyl > °3 allylic > 1°allylic
(B) 1°alkyl > 3° alkyl > °3 allylic > 1°allylic > methyl
(C) methyl > 1°alkyl > 1°allylic > 3° alkyl > °3 allylic
(D) methyl > 1°alkyl > 1°allylic > °3 allylic > 3° alkyl
(E) methyl > 1°allylic > 1°alkyl > 3° alkyl > °3 allylic
C
(4) What is the predominant product in the following reaction?
Cl
B
Hofmann Rule
KOC(CH3)3
(A)
(B)
(C)
(D)
OC(CH3)3
(5) What is the major product of reacting (S)-2-bromopentane with sodium cyanide? H Br
(A)
(B)
(C)
(D)
H C N
H C N
B
(6) The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the
effect of doubling the concentration of NaI on the rate of the reaction?
(A) The rate is halved
(B) The rate increases by a factor of 2
(C) The rate increases by a factor of 4 (D)The rate remains the same
(7) Which of the following alkyl halides reacts most slowly with NaN3 in dimethylsulfoxide?
(A)
(B)
(C)
(D)
Br
Br
Br
Br
H3C
B
A
(8) Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium
methoxide, NaOCH3?
(A) 1-bromobutane (B) 1-iodobutane (C) 1-fluorobutane (D) 1-chlorobutane
B
(9) Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium
cyanide, NaCN?
(A) bromomethane (B) bromoethane (C) 2-bromopropane (D) tert-butyl bromide
A
page 1 of 2
CHM 2210 Problem Set 9
problem 19:
disobeys
Zaitsev
(10) In which of the following solvents would the reaction of 1-bromobutane with sodium
chloride, NaCl, proceed the fastest?
(A) methanol (B) acetonitrile (D) water (D) acetic acid
(11) Which of the following anions is the most nucleophilic in polar protic solvents?
(A) fluoride anion (B) chloride anion (C) bromide anion (D) iodide anion
student#
letter
B
D
(12) Which of the following undergoes the most rapid reaction with methyl iodide?
(A) methoxide anion (B) acetate anion (C) chloride anion (D) water
A
(13) Which of the following alkyl halides undergoes the fastest hydrolysis
(i.e., substitution reaction with water)?
(A) bromomethane (B) bromoethane (C) tert-butyl bromide (D) 2-bromopropane
(14) Which of the following energy diagrams best represents the course of an exothermic
SN1 reaction? (A) 1 (B) 2 (C) 3 (D) 4
C
(15) What is the major product of the reaction of (R)-3-chloro-3-methylhexane with
water, H2O? (A) (R) 3-methyl-3-hexanol
(B) (S) 3-methyl-3-hexanol
(C) racemic 3-methyl-3-hexanol (D) (E) 3-methyl-3-hexene
Cl
(16) What is the major organic product obtained from the reaction of 2-bromo-2methylbutane with sodium methoxide in methanol?
Br
Br
(A)
(B)
(C)
(D)
O
C
OMe
(17) Which is not a product possible by heating (bromomethyl)cyclobutane in methanol?
(A)
(B)
(C)
(D)
Br
OMe
(18) How many elimination products are possible with 3-bromo-3-methylhexane? (Don't
forget cis/trans isomers.)
Br
(A) 1 (B) 2 (C) 3 (D) 4 (E) 5 (F) 6 (G) 7 (H) 8 (I) 9 (J) 10
(19) How many elimination products are possible with 3-bromo-3-methylhexane that obey
Zaitsev's Rule?
see structres above
(A) 1 (B) 2 (C) 3 (D) 4 (E) 5 (F) 6 (G) 7 (H) 8 (I) 9 (J) 10
(20) What is the major product of E2 elimination from trans-1-bromo-2-methylcyclohexane?
(A)
(B)
(C)
(D)
Br
A
B
C
E
D
C
H
CH3 page 2 of 2